ethyl (S)-2-oxo-1-vinylcyclopentanecarboxylate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (S)-2-oxo-1-vinylcyclopentanecarboxylate
• 英文别名: ethyl (1S)-1-ethenyl-2-oxocyclopentane-1-carboxylate
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: IWGJKMSPAVRWMQ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 2-[(2S,3R)-1-methoxy-3-methylpentan-2-ylamino]cyclopent-1-enecarboxylate 、 乙炔 在 indium(III) triflate 、 正丁基锂 、 3 A molecular sieve 、 溶剂黄146 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 120.0 ℃ 、101.33 kPa 条件下， 反应 33.0h， 生成 ethyl (R)-2-oxo-1-vinylcyclopentanecarboxylate 、 ethyl (S)-2-oxo-1-vinylcyclopentanecarboxylate
  参考文献：
  名称：

  Construction of a Chiral Quaternary Carbon Center by Indium-Catalyzed Asymmetric α-Alkenylation of β-Ketoesters

  摘要：

  Construction of a nonracemic all-carbon quaternary stereocenter at the a-position of beta-ketoesters was achieved by way of an indium(III)-catalyzed diastereoselective alpha-alkenylation reaction of chiral enamines with 1-alkynes. The enamine bearing a chiral auxiliary derived from L-isoleucine was added to the alkyne to give an alpha-alkenylated product in excellent yield and with a stereoselectivity better than 90% ee. One can ascribe the high selectivity to a chelate intermediate involving the auxiliary and the metal atom and the high yield to efficient interactions between the indium(III) atom and the alkyne. The selectivity increased as the reaction temperature was raised to 120 degrees C and decreased at higher temperatures.

  DOI：

  10.1021/ja710408f